Triethylamine → 1-[(S)-2-Hydroxy-1-oxopropyl]-L-proline, phenylmethyl ester

HRID 2290231Notes

Reaction equation

HRID 2290231 reaction equation
[C:1]([O-])(=[O:5])[CH:2]([CH3:4])[OH:3].[Na+].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.C(N(CC)CC)C.Cl.[NH:33]1[CH2:47][CH2:46][CH2:45][C@H:34]1[C:35]([O:37][CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)=[O:36]>CN(C=O)C>[OH:3][C@@H:2]([CH3:4])[C:1]([N:33]1[CH2:47][CH2:46][CH2:45][C@H:34]1[C:35]([O:37][CH2:38][C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1)=[O:36])=[O:5]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 2733413Proline benzyl ester hydrochlorideHCID 23666456Sodium Lactate

Product 1

HCID 133352881-[(S)-2-Hydroxy-1-oxopropyl]-L-proline, phenylmethyl esterYield 60%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of sodium lactate (1.7 g, 15.0 mmole), diphenyl phosphorylazide (3.6 ml, 16.5 mmole) and dry DMF (30 ml) at 0° C. (ice bath) in an argon atmosphere was treated with triethyl amine (2.1 ml, 15.2 mmole) and L-proline, phenylmethyl ester, hydrochloride salt (3.6 g, 15.0 mmole). After 24 hours, the reaction mixture was partitioned between EtOAc and H2O. The aqueous phase was back extracted, the organic extracts combined, washed with 5% KHSO4, brine, and evaporated. The residue (5.0 g) was chromatographed on silica (130 g) eluting with EtOAc/Hexane (1:1) to give the title compound (2.5 g, 9.0 mmole, 60% yield) as a white crystalline solid after evaporation, m.p. 86°-88° C.

Workup

  1. customthe reaction mixture was partitioned between EtOAc and H2O
  2. extractionThe aqueous phase was back extracted
  3. washwashed with 5% KHSO4, brine
  4. customevaporated
  5. customThe residue (5.0 g) was chromatographed on silica (130 g)
  6. washeluting with EtOAc/Hexane (1:1)

Sources & evidence

ORD record
ord-0f6880680366401291eb4d1ff1d0be15
Source dataset
uspto-grants-1986_10
Patent number
US04616005

Reaction notes

Loading…